반응 #86637

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DIPEA

Carboxylic acid

(S)-2-[(S)-3-(4-Allyloxy-phenyl)-2-tert-butoxycarbonylamino-propionylamino]-4-methyl-pentanoic acid

HATU

EtOAc

→

(S)-2-{(S)-2-[(S)-3-(4-Allyloxy-phenyl)-2-tert-butoxycarbonylamino-propionylamino]-4-methyl-pentanoylamino}-pent-4-enoic acid methyl ester

용매

DMF

반응 조건

후처리

1. 1
   기타before being partitioned between EtOAc and 1M hydrochloric acid
2. 2
   세척The organic phase was washed sequentially with 1M hydrochloric acid and brine
3. 3
   건조before being dried (MgSO4)
4. 4
   여과filtered
5. 5
   농축concentrated in vacuo
6. 6
   기타Purification
7. 7
   세척eluting with a gradient of 1/3 EtOAc/(50/70) petroleum ether to 2/1 EtOAc/(50/70) petroleum ether
8. 8
   기타to yield a white solid, 1.40 g, 39%

실험 절차

Carboxylic acid 2 (2.86 g, 6.58 mmol), HATU (2.75 g, 7.24 mmol) and (S)-allyl-glycine methyl ester hydrochloride (1.20 g, 7.24 mmol) were dissolved in DMF (30 mL). DIPEA was added (4.60 mL, 26.4 mmol) and the reaction mixture was stirred at rt for 18 h before being partitioned between EtOAc and 1M hydrochloric acid. The organic phase was washed sequentially with 1M hydrochloric acid and brine before being dried (MgSO4), filtered and concentrated in vacuo. Purification was achieved using flash chromatography, eluting with a gradient of 1/3 EtOAc/(50/70) petroleum ether to 2/1 EtOAc/(50/70) petroleum ether to yield a white solid, 1.40 g, 39%. Rf=0.70 (1/1 EtOAc/(50/70) petroleum ether).

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